# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_[Mn]-1
_database_code_depnum_ccdc_archive 'CCDC 1939592'
loop_
_audit_author_name
_audit_author_address
'MAHENDRA KUMAR AWASTHI'
;Indian Institute Of Technology Indore
India
;
_audit_update_record             
;
2019-07-10 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H30 Mn N4 O4'
_chemical_formula_weight         481.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8681(13)
_cell_length_b                   9.0206(14)
_cell_length_c                   16.558(2)
_cell_angle_alpha                79.765(13)
_cell_angle_beta                 77.487(13)
_cell_angle_gamma                68.120(14)
_cell_volume                     1193.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1791
_cell_measurement_theta_min      3.7940
_cell_measurement_theta_max      24.0500

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             506
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8313
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.1004
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4310
_reflns_number_gt                2735
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1113P)²+0.0498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4310
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2405
_refine_ls_wR_factor_gt          0.1991
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.93345(9) 0.76079(8) 0.76245(5) 0.0446(3) Uani 1 1 d . . .
O2 O 1.1940(4) 0.7691(5) 0.7023(2) 0.0586(10) Uani 1 1 d . . .
O3 O 0.8206(5) 0.9736(4) 0.8155(3) 0.0621(11) Uani 1 1 d . . .
N1 N 0.7557(4) 0.6695(4) 0.7391(2) 0.0422(10) Uani 1 1 d . . .
O4 O 0.7624(5) 0.8283(5) 0.9306(3) 0.0759(13) Uani 1 1 d . . .
N3 N 1.0466(5) 0.5233(4) 0.8234(2) 0.0414(10) Uani 1 1 d . . .
O1 O 0.9866(4) 0.8624(5) 0.6346(2) 0.0615(11) Uani 1 1 d . . .
N2 N 0.5238(5) 0.6536(5) 0.7222(3) 0.0487(11) Uani 1 1 d . . .
H2N H 0.4232 0.6816 0.7151 0.058 Uiso 1 1 calc R . .
C10 C 0.6320(6) 0.5001(6) 0.7286(3) 0.0469(12) Uani 1 1 d . . .
C3 C 0.7502(6) 0.9611(6) 0.8902(4) 0.0494(13) Uani 1 1 d . . .
N4 N 1.1627(5) 0.3301(5) 0.9142(3) 0.0479(11) Uani 1 1 d . . .
H4N H 1.2167 0.2797 0.9540 0.058 Uiso 1 1 calc R . .
C6 C 1.0953(6) 0.2640(6) 0.8687(3) 0.0412(11) Uani 1 1 d . . .
C23 C 1.0222(7) 0.2933(7) 0.5982(4) 0.0596(15) Uani 1 1 d . . .
H23 H 0.9392 0.2493 0.6118 0.072 Uiso 1 1 calc R . .
C9 C 0.7757(6) 0.5098(5) 0.7387(3) 0.0401(11) Uani 1 1 d . . .
C18 C 1.0517(6) 0.3636(5) 0.6582(3) 0.0410(12) Uani 1 1 d . . .
C11 C 0.5991(6) 0.7538(6) 0.7287(3) 0.0491(13) Uani 1 1 d . . .
C8 C 0.9408(5) 0.3755(5) 0.7442(3) 0.0393(11) Uani 1 1 d . . .
H8 H 0.9173 0.2752 0.7582 0.047 Uiso 1 1 calc R . .
C19 C 1.1774(6) 0.4246(6) 0.6366(3) 0.0520(14) Uani 1 1 d . . .
H19 H 1.2011 0.4716 0.6756 0.062 Uiso 1 1 calc R . .
C4 C 0.6478(8) 1.1125(7) 0.9291(4) 0.079(2) Uani 1 1 d . . .
H4B H 0.6321 1.0895 0.9886 0.119 Uiso 1 1 calc R . .
H4C H 0.5426 1.1557 0.9109 0.119 Uiso 1 1 calc R . .
H4A H 0.7029 1.1894 0.9129 0.119 Uiso 1 1 calc R . .
C7 C 1.0244(5) 0.3844(5) 0.8124(3) 0.0373(11) Uani 1 1 d . . .
C14 C 1.1090(7) 0.0922(6) 0.8852(4) 0.0609(15) Uani 1 1 d . . .
H14A H 1.0413 0.0757 0.9372 0.091 Uiso 1 1 calc R . .
H14C H 1.2216 0.0258 0.8878 0.091 Uiso 1 1 calc R . .
H14B H 1.0729 0.0642 0.8413 0.091 Uiso 1 1 calc R . .
C17 C 0.5864(8) 0.3606(7) 0.7193(4) 0.0697(18) Uani 1 1 d . . .
H17A H 0.4808 0.3694 0.7525 0.105 Uiso 1 1 calc R . .
H17C H 0.6678 0.2622 0.7375 0.105 Uiso 1 1 calc R . .
H17B H 0.5814 0.3609 0.6619 0.105 Uiso 1 1 calc R . .
C5 C 1.1306(6) 0.4850(6) 0.8861(3) 0.0430(12) Uani 1 1 d . . .
C2 C 1.2471(8) 0.8535(9) 0.5563(4) 0.084(2) Uani 1 1 d . . .
H2A H 1.3360 0.7542 0.5460 0.126 Uiso 1 1 calc R . .
H2B H 1.2908 0.9336 0.5610 0.126 Uiso 1 1 calc R . .
H2C H 1.1858 0.8883 0.5110 0.126 Uiso 1 1 calc R . .
C21 C 1.2362(8) 0.3490(7) 0.4983(4) 0.0691(18) Uani 1 1 d . . .
H21 H 1.2973 0.3455 0.4449 0.083 Uiso 1 1 calc R . .
C20 C 1.2692(8) 0.4169(7) 0.5573(4) 0.0668(17) Uani 1 1 d . . .
H20 H 1.3542 0.4583 0.5439 0.080 Uiso 1 1 calc R . .
C1 C 1.1361(6) 0.8288(6) 0.6354(4) 0.0527(14) Uani 1 1 d . . .
C15 C 0.5175(8) 0.9305(7) 0.7240(4) 0.0711(18) Uani 1 1 d . . .
H15A H 0.3992 0.9559 0.7387 0.085 Uiso 1 1 calc R . .
H15B H 0.5523 0.9710 0.7645 0.085 Uiso 1 1 calc R . .
C12 C 1.1814(7) 0.6008(7) 0.9189(4) 0.0631(16) Uani 1 1 d . . .
H12A H 1.2167 0.6683 0.8720 0.076 Uiso 1 1 calc R . .
H12B H 1.0852 0.6699 0.9521 0.076 Uiso 1 1 calc R . .
C22 C 1.1122(9) 0.2866(7) 0.5190(4) 0.0741(19) Uani 1 1 d . . .
H22 H 1.0888 0.2398 0.4798 0.089 Uiso 1 1 calc R . .
C16 C 0.5546(12) 1.0130(9) 0.6407(5) 0.113(3) Uani 1 1 d . . .
H16B H 0.6686 1.0030 0.6295 0.170 Uiso 1 1 calc R . .
H16C H 0.4870 1.1246 0.6391 0.170 Uiso 1 1 calc R . .
H16A H 0.5324 0.9650 0.5994 0.170 Uiso 1 1 calc R . .
C13 C 1.3109(11) 0.5311(9) 0.9686(7) 0.159(5) Uani 1 1 d . . .
H13B H 1.2894 0.4467 1.0082 0.238 Uiso 1 1 calc R . .
H13C H 1.3150 0.6124 0.9976 0.238 Uiso 1 1 calc R . .
H13A H 1.4145 0.4879 0.9332 0.238 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O3 2.060(4) . ?
Mn1 N1 2.158(4) . ?
Mn1 N3 2.164(4) . ?
Mn1 O1 2.178(4) . ?
Mn1 O2 2.333(4) . ?
Mn1 C1 2.600(6) . ?
O2 C1 1.269(6) . ?
O3 C3 1.266(6) . ?
N1 C11 1.344(6) . ?
N1 C9 1.385(6) . ?
O4 C3 1.243(6) . ?
N3 C5 1.330(6) . ?
N3 C7 1.386(6) . ?
O1 C1 1.248(6) . ?
N2 C11 1.339(6) . ?
N2 C10 1.360(6) . ?
C10 C9 1.356(7) . ?
C10 C17 1.499(7) . ?
C3 C4 1.497(7) . ?
N4 C5 1.334(6) . ?
N4 C6 1.378(6) . ?
C6 C7 1.352(6) . ?
C6 C14 1.489(7) . ?
C23 C22 1.378(8) . ?
C23 C18 1.384(7) . ?
C9 C8 1.522(6) . ?
C18 C19 1.374(7) . ?
C18 C8 1.541(7) . ?
C11 C15 1.480(7) . ?
C8 C7 1.508(6) . ?
C19 C20 1.384(8) . ?
C5 C12 1.499(7) . ?
C2 C1 1.495(8) . ?
C21 C22 1.369(9) . ?
C21 C20 1.374(9) . ?
C15 C16 1.479(9) . ?
C12 C13 1.442(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Mn1 N1 111.64(15) . . ?
O3 Mn1 N3 127.79(16) . . ?
N1 Mn1 N3 86.14(15) . . ?
O3 Mn1 O1 97.76(15) . . ?
N1 Mn1 O1 95.28(15) . . ?
N3 Mn1 O1 130.29(14) . . ?
O3 Mn1 O2 103.11(15) . . ?
N1 Mn1 O2 138.76(15) . . ?
N3 Mn1 O2 89.81(14) . . ?
O1 Mn1 O2 57.68(14) . . ?
O3 Mn1 C1 103.34(16) . . ?
N1 Mn1 C1 117.65(17) . . ?
N3 Mn1 C1 110.75(16) . . ?
O1 Mn1 C1 28.58(15) . . ?
O2 Mn1 C1 29.17(14) . . ?
C1 O2 Mn1 87.2(3) . . ?
C3 O3 Mn1 115.1(3) . . ?
C11 N1 C9 105.8(4) . . ?
C11 N1 Mn1 127.3(3) . . ?
C9 N1 Mn1 126.7(3) . . ?
C5 N3 C7 106.4(4) . . ?
C5 N3 Mn1 127.2(3) . . ?
C7 N3 Mn1 125.8(3) . . ?
C1 O1 Mn1 94.8(4) . . ?
C11 N2 C10 108.9(4) . . ?
C9 C10 N2 106.3(4) . . ?
C9 C10 C17 131.9(5) . . ?
N2 C10 C17 121.6(5) . . ?
O4 C3 O3 121.9(5) . . ?
O4 C3 C4 120.1(6) . . ?
O3 C3 C4 117.9(5) . . ?
C5 N4 C6 108.8(4) . . ?
C7 C6 N4 105.7(4) . . ?
C7 C6 C14 132.3(5) . . ?
N4 C6 C14 122.0(4) . . ?
C22 C23 C18 122.0(6) . . ?
C10 C9 N1 109.2(4) . . ?
C10 C9 C8 128.7(4) . . ?
N1 C9 C8 122.0(4) . . ?
C19 C18 C23 117.5(5) . . ?
C19 C18 C8 123.0(4) . . ?
C23 C18 C8 119.5(5) . . ?
N2 C11 N1 109.8(4) . . ?
N2 C11 C15 123.4(5) . . ?
N1 C11 C15 126.8(5) . . ?
C7 C8 C9 114.0(4) . . ?
C7 C8 C18 113.3(4) . . ?
C9 C8 C18 110.2(4) . . ?
C18 C19 C20 120.8(5) . . ?
C6 C7 N3 109.2(4) . . ?
C6 C7 C8 127.8(4) . . ?
N3 C7 C8 122.9(4) . . ?
N3 C5 N4 109.9(4) . . ?
N3 C5 C12 124.2(5) . . ?
N4 C5 C12 125.9(5) . . ?
C22 C21 C20 119.1(6) . . ?
C21 C20 C19 120.8(6) . . ?
O1 C1 O2 120.1(5) . . ?
O1 C1 C2 119.5(6) . . ?
O2 C1 C2 120.4(5) . . ?
O1 C1 Mn1 56.6(3) . . ?
O2 C1 Mn1 63.7(3) . . ?
C2 C1 Mn1 172.2(4) . . ?
C16 C15 C11 113.1(6) . . ?
C13 C12 C5 116.3(5) . . ?
C21 C22 C23 119.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.110
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_[Mn]-2
_database_code_depnum_ccdc_archive 'CCDC 1939737'
loop_
_audit_author_name
_audit_author_address
'MAHENDRA AWASTHI'
;indian institute of technology indore
India
;
_audit_update_record             
;
2019-07-10 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Mn N4 O5'
_chemical_formula_weight         511.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1830(5)
_cell_length_b                   9.2736(5)
_cell_length_c                   16.6245(10)
_cell_angle_alpha                82.388(5)
_cell_angle_beta                 75.759(5)
_cell_angle_gamma                67.089(5)
_cell_volume                     1262.91(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5179
_cell_measurement_theta_min      3.4380
_cell_measurement_theta_max      27.7500

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             538
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9308
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.24
_reflns_number_total             4547
_reflns_number_gt                3909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.9863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4547
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1523
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.903
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.2614(2) 0.7230(3) 0.76955(14) 0.0547(6) Uani 1 1 d . . .
N2 N 0.9310(3) 0.8309(3) 0.76123(16) 0.0493(6) Uani 1 1 d . . .
H2N H 1.0320 0.8007 0.7617 0.059 Uiso 1 1 calc R . .
O1 O 0.4410(2) 0.6480(3) 0.84672(14) 0.0556(6) Uani 1 1 d . . .
O5 O 0.5555(4) 1.2064(3) 0.90149(16) 0.0729(8) Uani 1 1 d . . .
N4 N 0.3296(3) 1.1681(3) 0.58393(14) 0.0423(5) Uani 1 1 d . . .
H4N H 0.2860 1.2185 0.5433 0.051 Uiso 1 1 calc R . .
N1 N 0.6964(3) 0.8213(3) 0.76152(15) 0.0406(5) Uani 1 1 d . . .
N3 N 0.4218(3) 0.9769(3) 0.67279(14) 0.0366(5) Uani 1 1 d . . .
C8 C 0.5170(3) 1.1101(3) 0.76245(16) 0.0368(6) Uani 1 1 d . . .
H8 H 0.5377 1.2075 0.7560 0.044 Uiso 1 1 calc R . .
C11 C 0.3518(3) 1.0186(3) 0.60803(17) 0.0390(6) Uani 1 1 d . . .
O3 O 0.6510(3) 0.5322(3) 0.67283(17) 0.0682(7) Uani 1 1 d . . .
C18 C 0.3988(4) 1.1156(3) 0.84645(17) 0.0432(7) Uani 1 1 d . . .
C3 C 0.7278(4) 0.5465(4) 0.6004(2) 0.0502(7) Uani 1 1 d . . .
C10 C 0.3885(3) 1.2276(3) 0.63539(16) 0.0386(6) Uani 1 1 d . . .
C23 C 0.4267(4) 1.1632(3) 0.9164(2) 0.0554(8) Uani 1 1 d . . .
O4 O 0.7199(4) 0.6740(3) 0.56630(18) 0.0868(9) Uani 1 1 d . . .
C7 C 0.6789(3) 0.9774(3) 0.76089(16) 0.0370(6) Uani 1 1 d . . .
C17 C 0.3859(4) 1.3901(4) 0.6236(2) 0.0549(8) Uani 1 1 d . . .
H17A H 0.4257 1.4113 0.6672 0.082 Uiso 1 1 calc R . .
H17B H 0.2770 1.4626 0.6250 0.082 Uiso 1 1 calc R . .
H17C H 0.4534 1.4014 0.5709 0.082 Uiso 1 1 calc R . .
C6 C 0.8244(4) 0.9840(4) 0.76022(19) 0.0459(7) Uani 1 1 d . . .
C15 C 0.3046(4) 0.9133(4) 0.5672(2) 0.0539(8) Uani 1 1 d . . .
H15B H 0.4022 0.8287 0.5427 0.065 Uiso 1 1 calc R . .
H15A H 0.2405 0.8669 0.6096 0.065 Uiso 1 1 calc R . .
C1 C 0.3075(3) 0.6576(3) 0.83507(18) 0.0426(6) Uani 1 1 d . . .
C5 C 0.8512(3) 0.7368(3) 0.76143(19) 0.0464(7) Uani 1 1 d . . .
C9 C 0.4446(3) 1.1093(3) 0.69030(16) 0.0349(6) Uani 1 1 d . . .
C19 C 0.2640(4) 1.0773(4) 0.8567(2) 0.0536(8) Uani 1 1 d . . .
H19 H 0.2421 1.0484 0.8108 0.064 Uiso 1 1 calc R . .
C2 C 0.2062(4) 0.5889(5) 0.8998(2) 0.0641(9) Uani 1 1 d . . .
H2B H 0.2258 0.4852 0.8853 0.096 Uiso 1 1 calc R . .
H2C H 0.0940 0.6531 0.9033 0.096 Uiso 1 1 calc R . .
H2A H 0.2335 0.5843 0.9525 0.096 Uiso 1 1 calc R . .
C22 C 0.3214(6) 1.1648(4) 0.9941(2) 0.0736(13) Uani 1 1 d . . .
H16 H 0.3405 1.1938 1.0408 0.088 Uiso 1 1 calc R . .
C20 C 0.1603(5) 1.0808(5) 0.9334(2) 0.0746(11) Uani 1 1 d . . .
H18 H 0.0705 1.0540 0.9388 0.090 Uiso 1 1 calc R . .
C4 C 0.8373(5) 0.3978(5) 0.5567(3) 0.0811(12) Uani 1 1 d . . .
H4B H 0.8970 0.4230 0.5045 0.122 Uiso 1 1 calc R . .
H4C H 0.7734 0.3433 0.5473 0.122 Uiso 1 1 calc R . .
H4A H 0.9112 0.3325 0.5906 0.122 Uiso 1 1 calc R . .
C12 C 0.9305(4) 0.5621(4) 0.7644(3) 0.0665(10) Uani 1 1 d . . .
H12B H 0.9140 0.5218 0.7178 0.080 Uiso 1 1 calc R . .
H12A H 1.0461 0.5333 0.7583 0.080 Uiso 1 1 calc R . .
C13 C 0.8685(5) 0.4882(5) 0.8418(3) 0.0881(14) Uani 1 1 d . . .
H13A H 0.8772 0.5331 0.8884 0.132 Uiso 1 1 calc R . .
H13B H 0.9308 0.3777 0.8424 0.132 Uiso 1 1 calc R . .
H13C H 0.7572 0.5056 0.8450 0.132 Uiso 1 1 calc R . .
C24 C 0.5799(7) 1.2714(5) 0.9688(3) 0.0973(17) Uani 1 1 d . . .
H20A H 0.4885 1.3655 0.9853 0.146 Uiso 1 1 calc R . .
H20B H 0.6760 1.2952 0.9509 0.146 Uiso 1 1 calc R . .
H20C H 0.5914 1.1968 1.0149 0.146 Uiso 1 1 calc R . .
C21 C 0.1911(6) 1.1237(5) 1.0007(2) 0.0842(14) Uani 1 1 d . . .
H17 H 0.1222 1.1251 1.0522 0.101 Uiso 1 1 calc R . .
C14 C 0.8759(5) 1.1176(5) 0.7612(3) 0.0740(11) Uani 1 1 d . . .
H14A H 0.7896 1.2144 0.7526 0.111 Uiso 1 1 calc R . .
H14B H 0.9696 1.1075 0.7177 0.111 Uiso 1 1 calc R . .
H14C H 0.9016 1.1170 0.8139 0.111 Uiso 1 1 calc R . .
C16 C 0.2118(6) 0.9909(5) 0.5020(3) 0.0912(15) Uani 1 1 d . . .
H16C H 0.1090 1.0666 0.5266 0.137 Uiso 1 1 calc R . .
H16B H 0.1950 0.9138 0.4759 0.137 Uiso 1 1 calc R . .
H16A H 0.2710 1.0425 0.4612 0.137 Uiso 1 1 calc R . .
Mn1 Mn 0.52259(5) 0.74602(5) 0.72860(3) 0.04059(18) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.259(4) . ?
N2 C5 1.339(4) . ?
N2 C6 1.376(4) . ?
O1 C1 1.255(3) . ?
O1 Mn1 2.139(2) . ?
O5 C23 1.350(5) . ?
O5 C24 1.439(4) . ?
N4 C11 1.340(4) . ?
N4 C10 1.384(3) . ?
N1 C5 1.329(4) . ?
N1 C7 1.392(3) . ?
N1 Mn1 2.176(2) . ?
N3 C11 1.326(3) . ?
N3 C9 1.401(3) . ?
N3 Mn1 2.158(2) . ?
C8 C9 1.510(3) . ?
C8 C7 1.513(4) . ?
C8 C18 1.537(4) . ?
C11 C15 1.501(4) . ?
O3 C3 1.255(4) . ?
O3 Mn1 2.076(2) . ?
C18 C19 1.382(5) . ?
C18 C23 1.408(4) . ?
C3 O4 1.226(4) . ?
C3 C4 1.505(5) . ?
C10 C9 1.352(4) . ?
C10 C17 1.485(4) . ?
C23 C22 1.408(5) . ?
C7 C6 1.358(4) . ?
C6 C14 1.492(4) . ?
C15 C16 1.479(5) . ?
C1 C2 1.489(4) . ?
C5 C12 1.495(4) . ?
C19 C20 1.387(5) . ?
C22 C21 1.367(7) . ?
C20 C21 1.360(6) . ?
C12 C13 1.469(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N2 C6 108.6(2) . . ?
C1 O1 Mn1 97.60(18) . . ?
C23 O5 C24 117.4(3) . . ?
C11 N4 C10 108.6(2) . . ?
C5 N1 C7 106.2(2) . . ?
C5 N1 Mn1 127.34(19) . . ?
C7 N1 Mn1 123.77(17) . . ?
C11 N3 C9 106.0(2) . . ?
C11 N3 Mn1 128.60(18) . . ?
C9 N3 Mn1 124.59(17) . . ?
C9 C8 C7 112.5(2) . . ?
C9 C8 C18 112.3(2) . . ?
C7 C8 C18 112.1(2) . . ?
N3 C11 N4 110.4(2) . . ?
N3 C11 C15 124.9(3) . . ?
N4 C11 C15 124.7(3) . . ?
C3 O3 Mn1 112.4(2) . . ?
C19 C18 C23 118.0(3) . . ?
C19 C18 C8 122.9(2) . . ?
C23 C18 C8 119.1(3) . . ?
O4 C3 O3 122.8(3) . . ?
O4 C3 C4 120.2(4) . . ?
O3 C3 C4 117.0(3) . . ?
C9 C10 N4 105.7(2) . . ?
C9 C10 C17 132.3(3) . . ?
N4 C10 C17 122.0(2) . . ?
O5 C23 C22 125.3(3) . . ?
O5 C23 C18 115.1(3) . . ?
C22 C23 C18 119.6(4) . . ?
C6 C7 N1 109.1(2) . . ?
C6 C7 C8 129.1(3) . . ?
N1 C7 C8 121.8(2) . . ?
C7 C6 N2 105.8(3) . . ?
C7 C6 C14 132.4(3) . . ?
N2 C6 C14 121.7(3) . . ?
C16 C15 C11 115.0(3) . . ?
O1 C1 O2 120.4(3) . . ?
O1 C1 C2 118.7(3) . . ?
O2 C1 C2 120.9(3) . . ?
N1 C5 N2 110.2(3) . . ?
N1 C5 C12 127.1(3) . . ?
N2 C5 C12 122.6(3) . . ?
C10 C9 N3 109.3(2) . . ?
C10 C9 C8 128.7(2) . . ?
N3 C9 C8 122.0(2) . . ?
C18 C19 C20 121.9(3) . . ?
C21 C22 C23 119.8(3) . . ?
C21 C20 C19 119.3(4) . . ?
C13 C12 C5 113.2(3) . . ?
C20 C21 C22 121.4(4) . . ?
O3 Mn1 O1 95.23(10) . . ?
O3 Mn1 N3 129.62(10) . . ?
O1 Mn1 N3 130.20(9) . . ?
O3 Mn1 N1 107.47(9) . . ?
O1 Mn1 N1 99.14(9) . . ?
N3 Mn1 N1 87.92(8) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.053
